4-(4-Bromo­phen­yl)-6-(4-chloro­phen­yl)­pyrimidin-2-ylamine

Mujahid Hussain Bukhari; Hamid Latif Siddiqui; Naveed Ahmad; Waseeq Ahmad Siddiqui; Masood Parvez

doi:10.1107/S1600536809002748

. 2009 Jan 28;65(Pt 2):o390. doi: 10.1107/S1600536809002748

4-(4-Bromophenyl)-6-(4-chlorophenyl)pyrimidin-2-ylamine

Mujahid Hussain Bukhari ^a, Hamid Latif Siddiqui ^a,^*, Naveed Ahmad ^a, Waseeq Ahmad Siddiqui ^b, Masood Parvez ^c

PMCID: PMC2968275 PMID: 21581985

Abstract

The title compound, C₁₆H₁₁BrClN₃, contains pairs of molecules lying about inversion centers linked by amino–pyrimidine N—H⋯N hydrogen bonds. The eight-membered rings thus formed are represented by the R ₂ ²(8) motif in graph-set notation. The second H atom of the amine group shows a rather weak interaction with two Br atoms, resulting in bifurcated N—H⋯(Br,Br) hydrogen bonds. The dihedral angles between the mean planes of the benzene rings and the mean plane of the heterocyclic ring are 8.98 (15) and 35.58 (10)°. The Br and Cl atoms show substitutional disorder, with site-occupancy factors of 0.599 (2) and 0.401 (2), respectively.

Related literature

For related structures, see: Bukhari et al. (2008 ▶); Fun et al. (2006 ▶); Gallagher et al. (2004 ▶). For pharmacological activities of pyrimidines, see: Gangjee et al. (1999 ▶); Grivsky et al. (1980 ▶); Malik et al. (2006 ▶); Rao et al. (2003 ▶). For graph-set notation, see: Bernstein et al. (1994 ▶).

Experimental

Crystal data

C₁₆H₁₁BrClN₃
M _r = 360.64
Monoclinic,
a = 39.343 (8) Å
b = 3.851 (2) Å
c = 22.620 (6) Å
β = 123.81 (2)°
V = 2847.6 (18) Å³
Z = 8
Mo Kα radiation
μ = 3.07 mm⁻¹
T = 173 (2) K
0.20 × 0.03 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.579, T _max = 0.941
8088 measured reflections
2589 independent reflections
1944 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.094
S = 1.05
2589 reflections
203 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002748/fj2180sup1.cif

e-65-0o390-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002748/fj2180Isup2.hkl

e-65-0o390-Isup2.hkl^{(124.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Br1ⁱ	0.92 (4)	2.97 (4)	3.803 (4)	153 (3)
N3—H3A⋯Br1ⁱⁱ	0.92 (4)	3.11 (4)	3.540 (4)	111 (3)
N3—H3B⋯N2ⁱⁱⁱ	0.80 (4)	2.28 (5)	3.073 (5)	174 (4)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

Pyrimidines are a class of biologically active compounds having utility in the pharmaceutical and the agrochemical industries. Compounds with the ring system show pharmacological activity such as antitumor (Gangjee et al., 1999; Grivsky et al., 1980), antiviral (Rao et al., 2003), anti-HIV (Malik et al., 2006), etc. In continuation of our research work (Bukhari et al., 2008), we have prepared several pyrimidines. In this article, we report the crystal structure of the title compound, (I).

The structure of (I), (Fig. 1), contains dimeric pairs of molecules lying about inversion centers resulting from N3—H3B···N2ⁱⁱⁱ hydrogen bonds (N3···N2 = 3.071 (5) Å; Table 1 and Fig. 2). The 8-membered rings thus formed represent R₂²(8) motif in the graph set notation (Bernstein et al., 1994). The second H-atom of the amine, N3A, shows rather week interactions with two Br atoms representing bifurcated hydrogen bonds (H3A···Br1 2.97 (4) and 3.11 (4) Å). The mean-planes of the two phenyl rings, C5—C10 and C11—C16, are oriented with respect to the mean-plane of the heterocyclic ring at 8.98 (15) and 35.58 (10)°, respectively. The molecular dimensions in (I) agree with the corresponding molecular dimensions reported for 4,6-(diphenyl)pyrimidin-2-amine (Gallagher et al., 2004; Fun et al., 2006). The structure is devoid of any C—H···π(arene) contacts observed in the structures reported above.

Experimental

The title compound was synthesized by the procedure reported earlier (Bukhari et al., 2008). Crystals of (I) suitable for crystallographic analysis were grown by slow evaporation at 313 K from a solutuion of CHCl₃ (Yield 58%; m.p. 512–514 K).